3-(2-(undecyloxy)phenyl)propanoic Acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(2-(undecyloxy)phenyl)propanoic Acid
• 英文别名: 3-(2-Undecoxyphenyl)propanoic acid；3-(2-undecoxyphenyl)propanoic acid
• 化学式: C₂₀H₃₂O₃
• 分子量: 320.472
• InChiKey: NKRNIFVCTKMEES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-(undecyloxy)phenyl)propanoic Acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 35.0h， 生成 (2S)-2-amino-3-(hydroxy{(3R,4R)-4-[3-(2-undecyloxy-phenyl)propionyloxy]tetrahydro-pyran-3-yloxy}phosphoryloxy)propionic acid acetic acid
  参考文献：
  名称：

  Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors

  摘要：

  Lysophosphatidylserine (LysoPS), an endogenous ligand of G protein-coupled receptors, consists of L-serine, glycerol, and fatty acid moieties connected by phosphodiester and ester linkages, respectively. An ester linkage of phosphatidylserine can be hydrolyzed at the 1-position or at the 2-position to give 2-acyl lysophospholipid or 1-acyl lysophospholipid, respectively. 2-Acyl lysophospholipid is in nonenzymatic equilibrium with 1-acyl lysophospholipid in vivo. On the other hand, 3-acyl lysophospholipid is not found, at least in mammals, raising the question of whether the reason for this might be that the 3-acyl isomer lacks the biological activities of the other isomers. Here, to test this idea, we designed and synthesized a series of new 3-acyl lysophospholipids. Structure- activity relationship studies of more than 100 "glycol surrogate" derivatives led to the identification of potent and selective agonists for LysoPS receptors GPR34 and P2Y10. Thus, the non-natural 3-acyl compounds are indeed active and appear to be biologically orthogonal with respect to the physiologically relevant 1- and 2-acyl lysophospholipids.

  DOI：

  10.1021/acs.jmedchem.0c01126
• 作为产物：
  描述：

  1-溴十一烷 在 caesium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 12.0h， 生成 3-(2-(undecyloxy)phenyl)propanoic Acid
  参考文献：
  名称：

  リゾホスファチジルセリン誘導体

  摘要：

  【目标】本发明的目的是提供磷脂酰丝氨酸衍生物或其盐。 【解决方法】根据本发明，提供了磷脂酰丝氨酸衍生物或其盐，或者包含该化合物或其盐的药物组成物或磷脂酰丝氨酸受体功能调节剂。 【选定图】无

  公开号：

  JP2016017036A

文献信息

• リゾホスファチジルセリン誘導体
  申请人：国立大学法人 東京大学

  公开号：JP2016017036A

  公开（公告）日：2016-02-01

  【課題】本発明の目的は、リゾホスファチジルセリン誘導体またはその塩を提供することである。【解決手段】本発明により、リゾホスファチジルセリン誘導体またはその塩、または、当該化合物またはその塩を含む、医薬組成物またはリゾホスファチジルセリン受容体機能調節剤が提供される。【選択図】なし

  【目标】本发明的目的是提供磷脂酰丝氨酸衍生物或其盐。 【解决方法】根据本发明，提供了磷脂酰丝氨酸衍生物或其盐，或者包含该化合物或其盐的药物组成物或磷脂酰丝氨酸受体功能调节剂。 【选定图】无
• COMPOUND HAVING LYSOPHOSPHATIDYLSERINE RECEPTOR FUNCTION MODULATION ACTIVITY
  申请人：The University of Tokyo

  公开号：EP2952517B1

  公开（公告）日：2018-03-07
• Conformational Constraint of the Glycerol Moiety of Lysophosphatidylserine Affords Compounds with Receptor Subtype Selectivity
  作者：Sejin Jung、Asuka Inoue、Sho Nakamura、Takayuki Kishi、Akiharu Uwamizu、Misa Sayama、Masaya Ikubo、Yuko Otani、Kuniyuki Kano、Kumiko Makide、Junken Aoki、Tomohiko Ohwada

  DOI：10.1021/acs.jmedchem.5b01925

  日期：2016.4.28

  Lysophosphatidylserine (LysoPS) is an endogenous lipid mediator that specifically activates membrane proteins of the P2Y and its related families of G protein coupled receptors (GPCR), GPR34 (LPS1), P2Y10 (LPS2), and GPR174 (LPS3). Here, in order to increase potency and receptor selectivity, we designed and synthesized LysoPS analogues containing the conformational constraints of the glycerol moiety. These reduced structural flexibility by fixation of the glycerol framework of LysoPS using a 2-hydroxymethyl-3-hydroxytetrahydropyran skeleton, and related structures identified compounds which exhibited high potency and selectivity for activation of GPR34 or P2Y10. Morphing of the structural shape of the 2-hydroxymethyl-3-hydroxytetrahydropyran skeleton into a planar benzene ring enhanced the P2Y10 activation potentcy rather than the GPR34 activation.
• LYSOPHOSPHATIDYLSERINE DERIVATIVE
  申请人：THE UNIVERSITY OF TOKYO

  公开号：US20170210767A1

  公开（公告）日：2017-07-27

  An object of the present invention is to provide a lysophosphatidylserine derivative or a salt thereof. The present invention provides a lysophosphatidylserine derivative or a salt thereof, or a pharmaceutical composition or a lysophosphatidylserine receptor function modulator comprising said compound or a salt thereof.
• US9856278B2
  申请人：——

  公开号：US9856278B2

  公开（公告）日：2018-01-02